Nitrogen → HCID 59314094, compound

HRID 1047950Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2I)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:16])[C:12]=2[F:15])[CH2:7]1)=[O:5])[CH3:2].[CH3:28][C:29]([CH3:40])=[CH:30]B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+].N#N>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1([NH:17][C:18](=[O:27])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2[CH:28]=[C:29]([CH3:40])[CH3:30])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:16])[C:12]=2[F:15])[CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-(4,5-difluoro-2-(2-iodo-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (386) (2.55 g, 5.25 mmol) and 2-methyl-1-propenyl boronic acid pinacol ester (364 mg, 10.5 mmol) in dioxane (100 mL) is added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (350 mg, 8.2% mmol) and 2M aqueous solution of K2CO3 (7.87 mL, 15.75 mmol). The resulting reaction mixture is filled in with N2, heated to 100° C. and stirred continuously for 6 h. Reaction mixture is filtered and concentrated in vacuo, and the resulting residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-50% EtOAc in heptane) to give a pure product (387) as light brown solid (1.24 g, 57%).

Workup

customThe resulting reaction mixture
customReaction mixture
filtrationis filtered
concentrationconcentrated in vacuo
customthe resulting residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0%-50% EtOAc in heptane)

Sources & evidence

ORD record: ord-8a88783f63d94568a9684760f145ab40
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569535B2

Reaction notes

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